Winchester Home Values and Market Report
| Address | Beds | Baths | Living ft2 | List Price | Cost per ft2 | DOM |
|---|---|---|---|---|---|---|
| 398 Scofield Mountain Rd | 4 | 6 | 5,120 | $3,995,000 | $780 | Unknown |
| 00 Rte 10 | N/A | N/A | N/A | $2,100,000 | Unknown | Unknown |
| 27 Headlands Rd | 2 | 2 | 1,351 | $715,000 | $529 | Unknown |
| 39 Headlands Rd | 3 | 2 | 1,364 | $698,000 | $511 | Unknown |
| 60 Forest Lake Rd | 2 | 2 | 1,676 | $650,000 | $387 | Unknown |
| 295 Manning Hill Rd | 3 | 2 | 2,671 | $599,900 | $224 | Unknown |
| 484 Scofield Mountain Rd | 3 | 2 | 2,516 | $599,000 | $238 | Unknown |
| 166 Keene Rd | 3 | 2 | 1,808 | $479,900 | $265 | Unknown |
| 71 Headlands Rd | 3 | 2 | 1,066 | $445,000 | $417 | Unknown |
| 253 Back Ashuelot Rd | 1 | 1 | 1,290 | $425,000 | $329 | Unknown |
| Average: | 2.7 | 2.0 | 2,072 | $529,123 | $285 | N/A day |
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| Address | Beds | Baths | Living ft2 | List Price | Cost per ft2 | DOM |
|---|---|---|---|---|---|---|
| 418 Forest Lake Rd | 2 | 2 | 1,392 | $499,900 | $359 | Unknown |
| 305 Richmond Rd | N/A | N/A | 2,790 | $475,000 | $170 | Unknown |
| 55 Verry Brook Rd | 3 | 2 | 1,192 | $359,500 | $301 | Unknown |
| 229 Back Ashuelot Rd | 2 | 1 | 960 | $324,900 | $338 | Unknown |
| Map 6 Map 6 Opportunity Dr | N/A | N/A | N/A | $131,600 | Unknown | Unknown |
| Map 6 Lot 15-0 Map 6 | N/A | N/A | N/A | $118,200 | Unknown | Unknown |
| Map 6 Lot 15-8 Map 6 | N/A | N/A | N/A | $117,500 | Unknown | Unknown |
| Average: | 2.3 | 1.7 | 1,583 | $289,514 | $292 | N/A day |
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| Address | Beds | Baths | Acres | Living ft2 | List Price | Sold Price | Cost per ft2 | Sold Date | Acres |
|---|---|---|---|---|---|---|---|---|---|
| 463 Old Spofford Rd | 3 | 4 | 23.59 | 3,423 | $849,000 | $849,000 | $248 | 10/16/25 | 23.59 |
| 259 Bolton Rd | 3 | 2 | 1.8900000000000001 | 3,472 | $849,900 | $830,000 | $239 | 5/15/26 | 1.8900000000000001 |
| 130 Watson Rd | 3 | 2 | 12 | 2,145 | $694,900 | $750,000 | $349 | 4/22/26 | 12 |
| 73 Lake Shore Dr | 4 | 3 | 0.73 | 2,975 | $749,900 | $729,900 | $245 | 1/6/26 | 0.73 |
| 679 Warwick Rd | 4 | 2 | 137.55 | 2,946 | $599,900 | $599,900 | $203 | 10/17/25 | 137.55 |
| 583 Burt Hill Rd | 5 | 3 | 1.67 | 3,114 | $549,800 | $560,000 | $179 | 3/31/26 | 1.67 |
| 15 High St | N/A | N/A | 0.68 | 4,519 | $550,000 | $550,000 | $121 | 8/6/26 | 0.68 |
| 49 Old Mtn Turnpike Rd | 3 | 2 | 1.16 | 1,528 | $599,000 | $540,000 | $353 | 7/31/26 | 1.16 |
| 510 Old Westport Rd | 3 | 2 | 4.75 | 1,930 | $549,900 | $537,500 | $278 | 11/18/25 | 4.75 |
| 406 Back Ashuelot Rd | N/A | N/A | 1.8 | 5,321 | $530,000 | $535,000 | $100 | 7/27/26 | 1.8 |
| Average: | 2.9 | 2.0 | 1,831 | $309,263 | $300,031 | $202 | |||
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Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated .